Ethanol → 4-(2-carboxyethyl)-3-methyl-5-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid

HRID 24534

Reaction equation

HRID 24534 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]([CH:18]=[C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]2=[O:28])=[C:9]([CH2:12][CH2:13][C:14]([O:16]C)=[O:15])[C:10]=1[CH3:11])=[O:5])C.[OH-].[K+].C(O)C.O>C(O)(=O)C>[C:14]([CH2:13][CH2:12][C:9]1[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[NH:7][C:8]=1[CH:18]=[C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][C:20]1=[O:28])([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 537772934-(2-Methoxycarbonyl-ethyl)-3-methyl-5-(2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid ethyl ester

Product 1

HCID 536492844-(2-carboxyethyl)-3-methyl-5-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(2-Methoxycarbonylethyl)-3-methyl-5-(2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid ethyl ester (81.7 g)), 56.5 g of potassium hydroxide, 200 mL of ethanol and 200 mL of water were charged to a 1 L, 3 neck round bottom flask equipped with mechanical stirring and a thermometer. The mixture was stirred at 90° C. for 90 minutes, cooled to room temperature, and acidified with acetic acid until a precipitate formed. The precipitate was collected by vacuum filtration, washed with 50 mL of water and vacuum dried to give 69.1 g (85%) of 4-(2-carboxyethyl)-3-methyl-5-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid as a red solid.

Workup

  1. customequipped
  2. stirringThe mixture was stirred at 90° C. for 90 minutes
  3. customformed
  4. filtrationThe precipitate was collected by vacuum filtration
  5. washwashed with 50 mL of water and vacuum
  6. customdried

Sources & evidence

ORD record
ord-c1f2c99307e44b8394c7ee6ac810f369
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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